Curable coating compositions containing carbamate functional reactive additives

Abstract

The invention thus provides a curable coating composition comprising (A) a polymer resin comprising active hydrogen-containing functional group other than carbamate, (B) a curing agent having groups that are reactive with said functional groups on (A), and (C) a reactive additive comprising at least one compound having a molecular weight of from 131 to 2000 and comprising at least one beta-hydroxy primary carbamate group and at least one alkyl group selected from the group consisting of straight chain alkyl groups of more than 10 carbons, branched alkyl groups of from 5 to 30 carbons, and mixtures thereof, wherein one or both of (A) and (B) comprise groups that are reactive with the primary carbamate group of (C). The invention also provides a method of making a preferred embodiment of the reactive additive (C) and the reactive additive (C).

We claim:  
     
       1. A curable coating composition comprising 
       (A) a polymer resin comprising active hydrogen-containing functional group other than carbamate,  
       (B) a curing agent having groups that are reactive with said functional groups on (A), and  
       (C) a reactive additive comprising at least one compound having a molecular weight of from 131 to 2000 and comprising at least one β-hydroxy primary carbamate group and at least one alkyl group selected from the group consisting of branched alkyl groups of from 5 to 30 carbons, straight chain alkyl groups of more than 10 carbons, and mixtures thereof, wherein one or both of (A) and (B) comprise groups that are reactive with the primary carbamate group of (C).  
     
     
       2. The curable coating composition of  claim 1  wherein the reactive additive (C) has only one carbamate group. 
     
     
       3. The curable coating composition of  claim 1  wherein the at least one alkyl group is a branched allyl group of from 8 to 12 carbons. 
     
     
       4. The curable coating composition of  claim 3  wherein the at least one alkyl group is a branched alkyl group of at least 10 carbons. 
     
     
       5. A curable coating composition comprising 
       (A) a polymer resin comprising active hydrogen-containing functional group other than carbamate,  
       (B) a curing agent having groups that are reactive with said functional groups on (A), and  
       (C) a reactive additive comprising at least one compound having a molecular weight of from 233 to 583 and having the formula:                    
       wherein X is a branched alkyl group of from 5 to 30 carbons, and one or both of (A) and (B) comprise groups that are reactive with the primary carbamate group of (C). 
     
     
       6. The curable coating composition of  claim 5  wherein the reactive additive (C) is only one carbamate compound. 
     
     
       7. The curable coating composition of  claim 5  wherein X is                    
       wherein one of R 1 , R 2  and R 3  is hydrogen and each of the remaining R 1 , R 2  and R 3  is an alkyl group of from 1 to 10 carbons. 
     
     
       8. The curable coating composition of  claim 7  wherein R 1 , R 2 , and R 3  total from 8 to 12 carbons with at least one of R 1 , R 2 , and R 3  being a methyl group. 
     
     
       9. The curable coating composition of  claim 7  wherein one of R 1 , R 2 , and R 3  is hydrogen. 
     
     
       10. A curable coating composition comprising 
       (A) a polymer resin comprising active hydrogen-containing functional group other than carbamate,  
       (B) a curing agent having groups that are reactive with said functional groups on (A), and  
       (C) a reactive additive comprising at least one compound having a molecular weight of from 131 to 2000 and having the formula:                    
       wherein R 1 , R 2 , and R 3  are each alkyl groups of from 1 to 10 carbons, and one or both of (A) and (B) comprise groups that are reactive with the primary carbamate group of (C). 
     
     
       11. The curable coating composition of  claim 10  wherein R 1 , R 2 , and R 3  total from 8 to 12 carbons with at least one of R 1 , R 2 , and R 3 being a methyl group.